Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols

被引：60

作者：

Arimitsu, Satoru ^{[1
]}

Jacobsen, Jesse M. ^{[1
]}

Hammond, Gerald B. ^{[1
]}

机构：

[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 07期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/jo800088y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iodocyclization of gem-difluorohomoallenyl and gem-difluorohomopropargyl alcohols with I-2 and ICI, respectively, produced the corresponding,fluorinated iodofuran analogues in good yields. The iodo substituent in fluorinated 4-iodofurans was utilized as a synthetic handle to prepare multisubstituted 3-fluorofurans using a Suzuki cross-coupling reaction. The yields of both iodocyclization of gem-difluorohomopropargyl alcohol and subsequent Suzuki coupling were dramatically enhanced by microwave irradiation.

引用

页码：2886 / 2889

页数：4

共 35 条

[1] Selective synthesis of fluorinated furan derivatives via AgNO3-catalyzed activation of an electronically deficient triple bond [J].

Arimitsu, Satoru ;

Hammond, Gerald B. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8559-8561

[2] gem-Difluoropropargylation of aldehydes using cat.: In/Zn in aqueous media [J].

Arimitsu, Satoru ;

Jacobsen, Jesse M. ;

Hammond, Gerald B. .

TETRAHEDRON LETTERS, 2007, 48 (09) :1625-1627

[3] Lanthanide triflate-catalyzed preparation of β,β-difluorohomopropargyl alcohols in aqueous media.: Application to the synthesis of 4,4-difluoroisochromans [J].

Arimitsu, Satoru ;

Hammond, Gerald B. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) :8665-8668

[4] A novel cyclization reaction between 2,3-bis(trimethylsilyl) buta-1,3-diene and acyl chlorides with straightforward formation of polysubstituted furans [J].

Babudri, Francesco ;

Cicco, Stefania R. ;

Farinola, Gianluca M. ;

Lopez, Linda C. ;

Naso, Francesco ;

Pinto, Vita .

CHEMICAL COMMUNICATIONS, 2007, (36) :3756-3758

[5] ELECTROPHILIC ADDITIONS OF POSITIVE IODINE TO ALKYNES THROUGH AN IODONIUM MECHANISM [J].

BARLUENGA, J ;

RODRIGUEZ, MA ;

CAMPOS, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3104-3106

[6] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].

Bellina, F ;

Carpita, A ;

Rossi, R .

SYNTHESIS-STUTTGART, 2004, (15) :2419-2440

[7] Solvent effect on intramolecular hydrogen bonds in push-pull conjugated molecules [J].

Bouchy, A ;

Rinaldi, D ;

Rivail, JL .

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2004, 96 (03) :273-281

[8]

DEAN FM, 1983, ADV HETEROCYCLIC CHE, V31, P273

[9] Practical alternatives for the synthesis of β-iodofurans by 5-endo-dig cyclisations of 3-alkyne-1,2-diols [J].

El-Taeb, GMM ;

Evans, AB ;

Jones, S ;

Knight, DW .

TETRAHEDRON LETTERS, 2001, 42 (34) :5945-5948

[10] Nucleophilic and electrophilic substitutions of difluoropropargyl bromides [J].

Hammond, Gerald B. .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (4-5) :476-488

← 1 2 3 4 →